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Things to Do in January in Chicago

Updated: September 27, 2023
 By Mel

This post covers the best things to do in Chicago this January, including, free, family-friendly, as well as nighttime activities, all updated for 2024.


January in Chicago is a great time to experience the city because it is a slow season for tourism. This means you won’t have to wait in lines or stand in crowds!

For some of the more popular things to do in Chicago, read the following posts:

1. Go to a Sporting Event

While January can be cold outside, cheering on your teams inside will keep you and your friends and family warm.

A number of teams will be playing home games this time of year.




Click here to see more sports events taking place in Chicago in January. 

2. Go to a Concert

If you are a music lover or a fan, be sure to check out a concert while in Chicago.

There are many venues in the Chicago area, from giant spaces to intimate bars.

Rock/Pop Concerts

Opera/Classical Concerts

Music Festivals

  • Tomorrow Never Knows | January 17th-21st | various locations | highlights a curated selection of up-and-coming indie artists

Click here to see more Chicago-area concerts happening in January.

3. Go on a Sightseeing Tour

Put on your parka and be sure to layer for our January tours!  Join our history-loving Chicago-adoring tour guides on foot.

We offer pay-what-you-like walking tours every day of the week in the Windy City. 

Try the Chicago Pedway tour to experience the indoor paths that run under the city, or the Winter Loop Tour for a winterized Loop experience.

If you’d prefer to enjoy a bus tour, we have a great comparison of Chicago’s best. From hop-on-hop-off buses to dedicated tours, you’ll find one to suit you here.

4. Go to the Theater

Chicago is home to many regional theaters, small black box spaces, and Broadway tour houses. There is something for everyone!  


Special Events


Check here for even more events in the Chicago area in January.

Pro-tip: Check out our self-guided theatre tour to admire the exterior of some of the oldest movie palaces in the downtown Loop.

5. Visit Let It Shine Lightshow

Grab your car (or a cab) and head to Chicago's North Shore for "Let it Shine," an immersive and creative lightshow.

Everyone can be immersed in the sight and sound of holidays from the comfort of their own vehicle (hence it's tagline, "a drive-though Christmas experience).

The lights are lit from November 17th, 2023 - January 8th, 2024.

Visit the "Let it Shine Lightshow" website for more information and ticket pricing.

For even more lights, visit the Illumination at the Morton Arboretum (until January 6th) or ZooLights at the Lincoln Park Zoo (until January 7th).

6. Enjoy a Stand-up Comedy Show

If you're in need of a good laugh, some of the most famous comedians in the world will be performing stand-up in the Chicago area this January.

Each of these performances is scheduled to take place either in Chicago or within around 30 minutes of the downtown area.

Comedy Shows

Comedy Clubs


Check here for a even more comedy shows taking place in Chicago in January.

7. Ice Skating in Downtown Chicago

Ice skating is a great way to spend the day or evening hours, especially with the numerous rinks around the city.

There is the McCormick Tribune Ice Rink in Millennium Park, open until early March.

Located right underneath Cloud Gate and on the edge of downtown, this is the perfect spot to skate (and keep warm with hot chocolate).

Across the bridge in Maggie Daley Park, you will find the Skating Ribbon

Surrounding the rock wall and with the skyline in the background, this experience aims to give you the feeling of skating through the alpines. 

For both rinks, skating is free, and rentals are on offer, usually around $12 on weekdays and $14 on weekends.

8. Take a Tour of a Local Brewery

Are you in Chicago and looking for a good local pint? Chicago is a great city to enjoy a local microbrew in one of our fantastic neighborhoods.

Many restaurants have enough space to brew their own beer, like Berghoff’s, Gino’s East, and Rock Bottom, but if you want to try multiple Chicago brews, these bars are great.  

Everyone has their favorite places for a pint, of course.

Click here for Chicago Brewery Tours!

9. Indulge in Chicago Food

Explore Chicago’s delicious food!

Head to a popular Chicago restaurant like Girl and the Goat to try Chef Stephanie Izzard’s amazing dishes. 

Another option is to head to one of our city's famous deep-dish places. Or head to Au Cheval for an amazing hamburger. 

Looking for a sweet treat? Try Stan’s Donuts with locally roasted coffee! 

If you are looking for something more casual, try a Chicago Hot dog or an Italian Beef sandwich!

10. See More for Less with a Chicago City Pass

Many of Chicago’s biggest attractions have entry fees. 

While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.

They can also save you time with skip-the-ticket-line privileges.

Each Chicago tourist discount pass includes a variety of fun activities and attractions.

Here are a few examples of what you can visit with a tourist pass, for a discount or for free.

For more details, make sure to read our full post covering Chicago tourist passes.

If you're already planning to buy a travel pass, you can purchase one here: All-Inclusive GoCity Pass | The Explorer GoCity Pass | Chicago CityPass

Honorable Mention: Chicago Restaurant Week

Traveling through your taste buds is always a fun thing to do when it is cold out! 

Chicago Restaurant Week (which usually falls in the last half of January and first part of February) is the perfect opportunity to try some of the best Chicago restaurants.  

Hundreds of restaurants participate during Restaurant Week, providing multiple-course meals with fixed-price menus.  

If nothing else, make sure you try some of the famous Chicago Style Deep Dish Pizza or enjoy a romantic fondue dinner.

But if you’re still hungry, sample your way with these self-guided food tours of Chicago neighborhoods.

On a budget? You can still get a taste of Chicago with some of the best cheap eats in the city. Or if you want to get a background with your brunch, take one of the best Chicago food tours. And when you’ve finished sampling, relax with something from a local coffee shop.


Chicago offers many free activities throughout the year. Here are a few suggestions during January.

Be sure to read our post about the top things to do in Chicago at night for even more suggestions.

Adler After Dark

During Wednesday hours, from 4:00 pm - 10:00 pm, Adler Planetarium opens up for a fun night-time event for adults. 

There are "hands-on, minds-on activities and experiences" that folks can enjoy along with their sky show.

It's a great way to escape the cold and enjoy the wonder of the universe.

Tickets must be purchased in advance.

Enjoy a Drag Show

Head to the South Loop to attend the Lips Drag show which has been around for more than 25 years.

They have performances Wednesday–Sunday, including a Sunday brunch! 

Check out the Local Music Scene

Check out the local music scene in Chicago and take a look at some of the more popular venues:

Go Out for a Cocktail

Chicago has more speakeasies – fitting for the mobster history of the Windy City.

If you’re looking for more than just atmosphere and want to find one of the best Craft Beers, we can make sure you find a local pint.

Go to a Game Bar

Explore some of Chicago’s best game bars. Whether you want to try an arcade bar with some pinball and Packman or try a classic board game, Chicago has a bar for you. 

Check out our favorite game bars across the city

Be sure to check out our post on top things to do in Chicago at night for even more suggestions.

Attend a Burlesque Show

Red Velvet Entertainment, known as Chicago's #1 variety and cabaret show, performs dance routines with burlesque dancers from around the world.

There is a lot of audience engagement, and the show changes from week to week.

Shows take place Thursday through Sunday at Y Bar.

More information can be found and tickets can be purchased, here.

Attend a Candlelight Concert

This concert series, taking place at various locations throughout Chicago, is truly magical.

Classical music is played by candlelight, creating an atmosphere that is both relaxing and enjoyable.

Concerts have included The Best of Hans Zimmer, a Tribute to ABBA, and a Tribute to Taylor Swift.

Tickets can be purchased here.


This section lists more free events, activities, and attractions so see in Chicago this month.

For more ideas, check out our post about the Top Free Things to Do in Chicago.

Take yourself out on a Self-Guided Food Tour

If you want to experience Chicago through your taste buds, try one of our self-guided food tours. 

Head to Chinatown to explore and enjoy savory buns and Peking duck. 

Pilsen is a wonderful neighborhood where you can appreciate the rich Mexican culture of the area while enjoying tasty dishes. 

Small but mighty Little Italy is definitely a neat neighborhood to experience too!

Get out of downtown to the northside neighborhood of Andersonville for a little shopping and tasty bites in the Swedish neighborhood.

The Bridgeport Art Center

Located in the Bridgeport building which is a creative home for local artists and designers, there is an outdoor sculpture garden and three curated art galleries. 

On the 3rd Friday of each month between 7:00 pm - 10:00 pm, people are invited to see the painters, sculptors, photographers work.

Free Chicago Walking Tours

Check out the Chicago Cultural Center

A great place to warm up while appreciating architecture is the Cultural Center. This beautiful and historic building is free and open for the public to explore.

Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here. 

This is also a great place for children’s programming.

Check out their calendar of events to see what is going on during your visit.

Go to Free Museums

There are many Chicago museums that are free! Check out our free museum list here.  

Also, if you happen to be a local traveler, be sure to check for free museum days during the winter months in Chicago.

For even more free activities, see our post on the top free things to do in Chicago.


Below we list several great options to keep your children entertained this month, including parks, museums, and theater!

Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.

See Light Up The Lake

Navy Pier’s Festival Hall transforms into an indoor holiday theme park called Light Up The Lake, with music, skating, carnival rides, and entertainment.

The dates haven't been released as of September 2023, though the event usually runs from November until the first week of January.

This is a great event for families with little kids, and children shorter than 3 feet tall are free to enter.

See a Light Show in the Garden 

Head a stretch north to the Chicago Botanic Garden to see the new event, Lightscape. The garden is transformed into a twinkly wonderland.

You walk on a one-mile path that includes majestic trees, water features, and stand-alone lighting installations.

The light show is active from November 10, 2023 - January 7th, 2024.  

Bring out Your Wizard

Open on select days and times throughout the month is Harry's Potter Magic at Play.

The hands-on experience is fun for all ages, taking place across three floors in Water Tower Place.

For additional information and tickets, visit the website.

Go to a Museum

January is a great month to have a few indoor options for the family in  Chicago so bringing the youngsters to an indoor museum is always a good idea!

Chicago has a lot of museums that are very interactive and ideal for kids such as:


About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: September 27th, 2023
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